The Messy Middle: Why Breakthrough Often Requires Discomfort

Two executives, months into a growing tension that’s begun to ripple across their teams, sit down for a long-overdue conversation.

I’m there to facilitate, hoping to help them finally surface the unspoken and move toward a resolution.

But what was meant to be a one-hour Zoom call stretches into its second hour. Voices are raised. Emotions spill over. Still no resolution in sight.

I’m thinking: “This isn’t going anywhere.”

But what if that moment of apparent failure—that uncomfortable, messy middle—isn’t a dead end, but the essential passage to breakthrough?

What if the very discomfort you’re trying to avoid is actually the doorway to your next level of growth?

The Illusion of Smooth Paths

We've been sold a myth about transformation—that it should be clean, efficient, and Instagram-worthy. A perfect arc from problem to solution.

But after 15+ years coaching some of the world's most successful founders, I've observed something different:

The most significant breakthroughs emerge from the messiest middles.

And while some leadership frameworks touch on crucial topics like presence, self-awareness, and emotional intelligence, few offer guidance for navigating the messy, uncomfortable transition states between where you are and where you want to be.

Today, I'm sharing a story that portrays the common necessity of discomfort and will transform how you approach the messy parts of your leadership journey.

When Conflict Resolution Doesn’t Seem to Work

Recently, a CEO client asked me to facilitate a conversation between two executives who weren't getting along. Their dysfunction was affecting the entire organization.

Tensions had been building for months. Communication had broken down. Their teams were starting to take sides.

When our meeting came, I created space for both executives to share their unfiltered truth. What followed wasn't pretty.

One executive revealed feeling consistently undermined and disrespected. The other felt their expertise was being ignored and their team unfairly criticized.

As accusations flew back and forth, I could feel the temperature in the room rising. Twenty minutes in, I was questioning my approach. An hour in, I was wondering if I was making things worse. Two hours in, we still had no clear resolution.

The session lasted 2.5 hours—far longer than planned. It was raw, uncomfortable, and ended without any neat resolution or heartwarming moment.

I left thinking I hadn't helped much at all.

The Surprising Aftermath

A week later, the CEO called: "Something shifted. They're working together better than they have in months."

I was stunned. From my perspective, the meeting had been a mess—uncomfortable, emotional, without clear closure.

"What happened?" I asked.

"It seems like they finally felt heard," the CEO explained. "Even though they were both taken aback at first hearing just how upset the other was, that honesty created space for actual understanding."

What I'd perceived as a professional failure had actually been exactly what was needed.

The messy, uncomfortable truth-telling—which didn’t feel good in the moment—was what allowed the relationship to thaw. Both executives finally felt seen in their frustration. Both had to sit with the discomfort of hearing hard truths.

The breakthrough wasn't immediate or pretty. It required them to move through discomfort rather than around it.

What I've Learned About Messy Middles

This experience was a powerful reminder for something I've observed repeatedly in my years coaching founders:

1. Transformation rarely looks like transformation while it's happening. In the moment, it often feels like confusion, failure, or chaos.
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2. Increased discomfort often precedes breakthrough. When things feel most uncomfortable, you're likely closest to the insight or shift you need.
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3. We try to rush past discomfort, but it's where the growth happens. Our instinct to avoid pain often prevents the very transformation we seek.
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4. The messiest conversations often yield the deepest connections. Superficial harmony maintains the status quo; productive discomfort creates change.

The Pattern of Unnecessary Worry

This insight about messy middles connects to another pattern I've noticed across dozens of clients: founders spend countless hours worrying about things not working out—raising money, hiring key roles, having tough conversations.

And then, remarkably often, things work out.

The founder who was certain they'd fail to close their round gets the term sheet.

The leader who agonized over firing an executive finds the conversation goes better than expected.

The team that seemed hopelessly divided finds common ground.

I often say to founders “What if it was always going to work out. You can spend all that energy worrying and then have it work out, or you can enjoy the journey and have it work out."

The lie our mind tells us is that worrying is what made it work out. From my experience, that’s rarely the case.

As Ram Dass wrote: "Worry and fear are not tickets on the express train, they are extra baggage. You were going that way anyway."

The messy middle—that period of uncertainty between taking action and seeing results—is where founders spend most of their emotional energy. But what if this uncomfortable space is actually where your leadership muscles develop?

Why This Matters for You

As founders and leaders, you face messy middles constantly:

• The search for product-market fit
• The period between product-market fit and scalability
• The awkward growth phase where systems break down
• The funding gap between rounds
• The leadership transition as you build an executive team

Your instinct will be to rush through these uncomfortable states. To reduce the discomfort through control, distraction, or premature solutions.

But what if being with these messy middles are exactly where your competitive advantage lies?

What if your ability to stay present, curious, and engaged during discomfort is what separates extraordinary leaders from merely good ones?

Practical Wisdom for Navigating Your Messy Middles

1. Recognize the pattern: Start noticing when you're in a messy middle—that uncomfortable space between where you were and where you want to be. Simply naming it can reduce reactivity.
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2. Welcome the discomfort: When you feel frustrated or anxious, try asking: "What if this discomfort is exactly what needs to be here right now?" This small shift can transform resistance into curiosity.
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3. Trust the process: Remember that your most significant past breakthroughs likely emerged from periods of greatest uncertainty or difficulty. This messy middle is no different.

The Breakthrough Is in the Discomfort

Remember:

• The breakthrough follows the uncomfortable conversation
• The clearest vision emerges after the period of confusion
• The strongest culture develops through resolving conflict, not avoiding it
• The most resilient leaders are forged in uncertainty, not certainty

The next time you find yourself in that uncomfortable gap between where you were and where you want to be, remember: you're not off track. You're exactly where transformation happens.

The messy middle isn't the obstacle to your breakthrough.

It is the path to your breakthrough.

With love,

- Dave Kashen

P.S. If you're currently navigating a messy middle in your leadership journey and want support moving through it with greater awareness and effectiveness, reply to this email. I'd love to hear what you're experiencing and might be able to offer some thoughts/advice.